3-呋喃基叠氮化物 | 113222-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 3-呋喃基叠氮化物
• 英文名称: 3-furoylazide
• 英文别名: furan-3-carboxylic acid-azide；Furan-3-carbonsaeure-azid；3-Furoyl-azide；Furan-3-carbonyl azide
• CAS: 113222-54-1
• 化学式: C₅H₃N₃O₂
• mdl: MFCD11637191
• 分子量: 137.098
• InChiKey: HEPRNHUAJNVNDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-呋喃基叠氮化物 生成 furan-3-yl isocyanate
  参考文献：
  名称：

  磁双稳态氮烯：单线态和三线态呋喃酰氮烯和三线态 3-呋喃基氮烯的基质分离

  摘要：

  通过相应叠氮化物的 266 nm 激光光解产生两种简单的酰基硝烯，2-呋喃酰硝基 (2) 和 3-呋喃酰硝基 (6)。两者在低温基质中都是磁双稳态的，这可以通过在固体 Ne、Ar、Kr、Xe 和 N2 基质 (3-40 K) 中用红外光谱直接观察闭壳单线态和在甲苯中的三线态来证明（ 10 K）与 EPR 光谱（32：|D/hc| = 1.48 cm-1 和 |E/hc| = 0.029 cm-1；36：|D/hc| = 1.39 cm-1 和 |E/hc|c = 0.039 cm-1)。随后的可见光和紫外激光照射分别导致异氰酸呋喃酯（3 和 7）和开环产物 3-氰基丙烯醛（9-E 和 9-Z）的形成，其中难以捉摸的 3-呋喃基腈 (38)还通过 IR 和 EPR 光谱（|D/hc| = 1.12 cm-1 和 |E/hc| = 0.005 cm-1）进行鉴定。

  DOI：

  10.1021/jacs.7b08957
• 作为产物：
  描述：

  3-糠酸 在 二苯基磷酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-呋喃基叠氮化物
  参考文献：
  名称：

  Synthesis and Biological Studies of a New Series of 5-Heteroarylcarbamoylaminopyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidines as Human A₃ Adenosine Receptor Antagonists. Influence of the Heteroaryl Substituent on Binding Affinity and Molecular Modeling Investigations

  摘要：

  Some pyrazolotriazolopyrimidines bearing different heteroarylcarbamoylamino moieties at the N5-position are described. We previously reported the synthesis of a water soluble compound with high potency and selectivity versus the human A(3) adenosine receptor as antagonist, and herein we present an enlarged series of compounds related to the previously mentioned one. These compounds showed A(3) adenosine receptor affinity in the nanomolar range and different levels of selectivity evaluated in radioligand binding assays at human A(1), A(2)A, A(2B), and A(3) adenosine receptors. In particular, the effect of the heteroaryl substituents at the N5 position has been analyzed. This study allows us to recognize that the presence of a pyridinium moiety in this position not only increases water solubility but also improves or retains potency and selectivity at the human A(3) adenosine receptors. In contrast, replacement of pyridine with different heterocycles produces loss of affinity and selectivity at the human A(3) adenosine receptors. A molecular modeling study has been carried out with the aim to explain these various binding profiles.

  DOI：

  10.1021/jm051147+

文献信息

• Visible Light-Induced Regioselective Cycloaddition of Benzoyl Azides and Alkenes To Yield Oxazolines
  作者：Peter Bellotti、Julien Brocus、Fatima El Orf、Mohamed Selkti、Burkhard König、Philippe Belmont、Etienne Brachet

  DOI：10.1021/acs.joc.9b00568

  日期：2019.5.17

  regioselective synthesis of oxazolines in high yields. The mild photosensitized manifold leverages the intermolecular formation of oxazolines with a wide functional group tolerance on both benzoyl azides and alkenes partners. Mechanistic investigations suggest the sensitization of the azide moiety as the key activation step.

  可见光催化作用可以高产率地进行恶唑啉的区域选择性合成。温和的光敏歧管利用分子间形成的恶唑啉在苯甲酰基叠氮化物和烯烃配偶体上具有宽泛的官能团耐受性。机理研究表明，叠氮化物部分的敏化是关键的活化步骤。
• Reaction of Amide and Sodium Azide for the Synthesis of Acyl Azide, Urea, and Iminophosphorane
  作者：Devaneyan Joseph、Sunwoo Lee

  DOI：10.1021/acs.orglett.2c02429

  日期：2022.8.26

  in DMF at 25 °C and produce the symmetrical ureas in THF/H2O at 80 °C via the sequential reaction of acyl substitution and Curtius rearrangement. All acyl azides were also obtained from the secondary amides via sequential reaction of p-toluenesulfonyl chloride and NaN3. In addition, keto-stabilized iminophosphoranes were prepared from a one-pot reaction of amides, NaN3, and phosphines.

  酰胺与 NaN 3在 25 °C 下在 DMF 中反应生成酰基叠氮化物，并在 80 °C 下通过酰基取代和 Curtius 重排的顺序反应在 THF/H 2 O 中生成对称脲。所有的酰基叠氮化物也是由仲酰胺通过对甲苯磺酰氯和NaN 3 的顺序反应得到的。此外，由酰胺、NaN 3和膦的一锅法反应制备了酮基稳定的亚氨基正膦。
• Orientation in the Furan Nucleus. VIII. β-Acylaminofurans
  作者：Robert R. Burtner

  DOI：10.1021/ja01318a037

  日期：1934.3
• Kuhn; Krueger, Chemische Berichte, 1956, vol. 89, p. 1473,1483
  作者：Kuhn、Krueger

  DOI：——

  日期：——
• BRIDSON J. N., CAN. J. CHEM., 1979, 57, NO 3, 314-317
  作者：BRIDSON J. N.

  DOI：——

  日期：——